Gray
by ChaosandMayhem
Summary: Kiyotaka Ishimaru has learned to see the world in stark black and white, and in a profession like his its easier that way. And he certainly never suspected that a notorious criminal like Mondo Oowada could show him how to blend that black and white, into a beautiful, dangerous gray. AU where everyone grew up and grew bitter, rated T for violence and Leon's potty mouth.
1. Dead Man's Gun

A/N: Hey everyone! Welcome to a little project of mine-the prompt "Person A is a bounty hunter hired to kill Person B, but winds up falling in love with them" was originally suggested to me on Tumblr, and it's blown up out of control. I've decided to start posting it here on FF as well, although updates will be more irregular (this is more a of pet project than anything else). And as always, a huge thank-you to Bel for patiently putting up with whatever I send her way for beta magic. :3

Eventually this will be Ishimondo. We just have to stop them from trying to kill each other first.

Enjoy!

EDIT: There are three typos in the summary that FF is being a butt about correcting. Hopefully they'll be better by tonight. ;A;

* * *

**Chapter 1: Dead Man's Gun**

The years had not been kind to Kiyotaka Ishimaru.

The 28-year-old slouched against the small wall on the rooftop building, unlit cigarette dangling idly from his lips. His odd red eyes bore down onto the small nightclub across the street. He was as still as a statue, and although he had been in this position for some time, Ishimaru had patience and stamina enough to last him several hours more. The only movement he made was to occasionally run his finger along the trigger of the sniper rifle he held in anticipation.

Hard work. Disciple. A strong moral code.

They had been all the right components for a Super High School Level Hall Monitor. And they were all the right components for a bounty hunter too.

The way Ishimaru saw it—the way he justified it to himself, privately—was that bounty hunters were simply the hall monitors of the real world. And this form of detention was just a bit more…permanent.

Once upon a time he had had a dream of being prime minister, of making a true difference in the world. But the world was crueler than any fifteen-year-old could suppose, and his grandfather's great failure dogged him no matter where he went, no matter how hard he worked. He had known hunger and poverty and crushing disappointment. Time and tribulations had rotted away his idealism, taken the shine from his eyes, but it had never robbed him of his goal.

He could still make a difference. He could still earn a new name for his family.

It was just going to take a lot more brute force than he had originally supposed.

Music blared from the night club and neon signs illuminated the patrons as they entered and exited the club in various states of inebriation, roaring with laughter and shouting insults and jests into the night.

Ishimaru's lip curled back in disgust.

His latest target had yet to leave the club; Ishimaru had seen him entering just as he had been setting up his position, but that had been several hours ago. Dimly he wondered just what one could do in a night club that could take so long—drink, eat peanuts, watch barely-legal girls strip for cash? His stomach roiled at the thought (sociability had never been Ishimaru's strong point, and the idea that people might be enjoying other people's company in there had never occurred to him).

Looking for a way to pass the time that did not involve watching a man retch on the sidewalk, Ishimaru slipped down behind the wall and pulled his target's dossier from his messenger bag.

_Mondo Oowada_, he read, _current leader of the Crazy Diamonds_.

Ishimaru read over the dossier with faint disinterest. The only thing of note to him was the fact that he and Oowada had apparently both attended the same high school, in the same year, no less.

Oowada's face—thug-like, heavy-lidded, scowling—did look vaguely familiar to Ishimaru, but he felt no sense of kinship to his former classmate. He was a notorious gang leader, a rabid dog that needed to be put down before he infected society.

Setting the dossier aside, Ishimaru dug a lighter out of his pocket and lit the cigarette in his mouth. Years ago he would have been horrified by the notion of smoking, of defiling the temple that was his body, but lately Ishimaru had found that smoking eased his nerves before a commission could be completed.

It never got any easier, killing, but what had to be done for the good of public morale had to be done in whatever way possible.

That's what he told himself, anyway.

"HEY!"

The baritone shout on the street made Ishimaru jump. He grabbed his rifle, cursing himself in low tones, and peered through the scope, scanning the streets below.

Oowada had finally emerged from the club, looking furious. His signature black coat was thrown over his shoulder, his ridiculous pompadour a mussed-up mess. He shoved his way through the crowd outside the door, striding forward in an intent to kill.

Ishimaru's finger tensed on the trigger.

"HEY! KID!"

Oowada had finally caught up with his target—a staggering, stumbling fellow some years his junior—grabbed him by the shoulder, and spun him around.

The drunkard blocked Ishimaru's clear shot. Frowning, he eased back and waited, watching the interaction between the two.

Oowada was nose-to-nose with the drunkard, howling so much that he was red in the face. He gesticulated wildly, demanding to know if the man was "fuckin' stupid or just suicidal" before snatching the motorcycle keys that had been dangling from the cretin's hand.

At that the drunkard sprang forward, protesting and cussing Oowada out, but the muscular gang leader just scowled and tucked the confiscated keys into his pocket.

Curious, Ishimaru tilted his head to the side, trigger finger idle.

The drunkard tried to swing a fist at Oowada, but that only earned him a cuff upside the head and more berating. As the drunkard staggered backwards, rubbing his head in pain, Oowada stepped off the block and onto the street, raising his arm.

After a minute a taxi rolled up. Oowada stepped forward, handed the driver some cash, and steered his drunken companion into the vehicle. He seemed to be making promises about the man's motorcycle: "Yeah, yeah, I'll get it to you tomorrow, relax. Just go home and sleep it off, jeez…"

Ishimaru was fascinated.

Oowada nodded at the driver before stepping back onto the sidewalk. He moved over to the brick wall beside the club, watching the entrance with intent etched into his features.

_Now_, a little voice urged Ishimaru, _now, while you have the chance!_

But it was now, of all the contracts he'd taken over the years, of all the criminals he'd killed, that Ishimaru found himself freezing up.

Time passed, Oowada did not moved, and still all Ishimaru could do was watch. As more members of Oowada's gang came stumbling out of the club, Oowada would stop them, checking each of them over personally. Those he deemed too inebriated to ride had their keys confiscated, and packed into a cab that he paid for himself.

Why? Ishimaru wanted to scream. Why are you doing this? You're a criminal, you're not supposed to care for other people, care about the consequences of their actions—!

Fury and bile rose in Ishimaru's throat. He'd spent a lifetime building the world in terms of black and white, and now this singular man, this gangster, was blending those colors. No, no there was no gray, there couldn't be gray, because if there was anything but black and white then he, the grandson of a prime minister, was more of a monster than that nobody criminal could ever be—!

He wanted Oowada dead, suddenly, dead and gone and not forcing him to question his moral code. Criminals couldn't be good men. They just couldn't be…

The fury left him, replaced by something heavy and sorrowful that didn't have a proper name.

Slowly he eased the rifle away, setting it down beside him. The cigarette was taken out of his mouth and crushed against the rooftop with a slight sizzle. He was tired, very tired, and he just wanted to go home.

He eased up—and froze.

For as he glanced down he could see, quite plainly, that Oowada's face was upturned towards the building opposite the club—_upturned towards him_.

The expression on Oowada's face was more curious than anything else, but Ishimaru didn't have time to consider what Oowada was thinking. He grabbed his items and bolted.

It was only later, as he lay awake on the cot he called a bed, that Ishimaru took the time to consider that perhaps Oowada had been expecting him to shoot.

* * *

The idea of an adult, embittered Ishimaru fascinates me, what can I say.

Thank you for reading!


	2. Rabbit Heart

Before we go any further, I do want to point that this isn't just gonna be "Ishimaru and Mondo Power Hour"-a lot of the DR and SDR2 cast will be showing up too. And I'll try to keep as many spoilers from SDR2 out of it as I can, but there are some roles that need to be fulfilled and, well, I'm only human.

Shocking, I know.

Enjoy!~

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_**Chapter Two: Rabbit Heart**_

The splash of tap water against his sweaty skin did a better job of rousing Ishimaru out of his tired stupor than anything else. He cupped his hands under the running faucet once more and splashed his face until his eyes were free from sleep.

One calloused hand reached up, turning off the water tap, but the faint _drip-drip-drip_ resounded through the empty flat. Ishimaru straightened with a sigh. Running one wet hand through his limp and greasy hair, he leaned up against the sink, inspecting himself in the cracked and lopsided mirror.

It had been an uneasy night. Half of him had been reliving the scene on the rooftop, and the other half had kept one ear cocked, listening for the inevitable break-in by the Crazy Diamonds and their thug leader, who would be looking to kill the would-be assassin.

Except there had been no break-in and his mental replays had left him with nothing but a vague dissatisfaction. His sleepless pallor made him look gray, with swaths of shadows cutting under his dull red eyes. Groaning, Ishimaru shoved himself off of the sink and stumbled out of the tiny bathroom, into his flat proper.

For a man who had had a once bright and prosperous future, his current living situation was abysmal. It was a one-room flat, just enough space for a cot, a chest of drawers, a mini fridge, and an old telephone. The wallpaper was an eyesore green, dulled by time and peeling in multiple places. The shades were drawn, blocking out the sounds of the city but also casting the room in dull gray light.

Mumbling under his breath, Ishimaru dragged a wrinkled shirt out of his chest and pulled it out. Old habits died hard, however, and he spent a few minutes tugging at the shirt in a vain attempt to ease the wrinkles out.

When his shirt look slightly more presentable, Ishimaru moved to the fridge, withdrew a carton of juice, and began to take long gulps. His stomach coiled, demanding food, and Ishimaru silently promised it he would grab a bagel from the deli down the street.

When orange juice had sated his stomach's grumbling, the bounty hunter collapsed back onto his cot and pulled his cell phone from his pocket. He held it for a moment, weighing the words in his mind, before pulling up a number and dialing.

**…**

His employer had not been pleased to find out that Mondo Oowada was still among the living, and Ishimaru had patiently received an earful before assuring the man on the other end that no, this deal wasn't beyond his abilities, and yes, the Crazy Diamonds would be searching for a new leader before the week was out.

Failure was not a word Ishimaru accepted into his vocabulary, even if it described him perfectly.

And so, with the gumption that had gotten him through high school, he decided to try again.

He spent the day shifting through old contacts and connections for some clue of Oowada's whereabouts, and when those results proved scant he decided to go back to the nightclub that night.

It was foolish to assume Oowada would be there—after all, in Ishimaru's experience once a man nearly got killed in one spot he wasn't liable to return. The best he had hoped for was some information from slovenly patrons, whether by coercion or a mild threat to have Chief Inspector Kirigiri down and around the club.

Mondo Oowada would not be back at the club; Mondo Oowada should not have been back at the club.

So that was why, when Ishimaru exited onto the rooftop of the building across the street from the club, the sight of a muscular frame standing at the edge was enough to stop him short.

The sound of the iron door slamming shut didn't garner the attention of the man, whose features were obscured by darkness. When Ishimaru's tentative "hello" didn't gain a response from the stranger either, Ishimaru took a few quick steps forward, tensing in case this man was about to jump.

"You're not supposed to be up here." Ishimaru's voice grew taunt. "It's against the rules."

A short snort served as the stranger's response.

"I'm serious! It's very dangerous!" His voice heightened. "You need to step away from there or—"

"Or what? You gonna give me a fuckin' detention slip? You know I always threw those away, right?"

Ishimaru froze. What little color he had drained away as Mondo slowly pivoted on the spot, flashing him a wicked grin. "Hall Monitor," he growled. "Still chasing me after all these years."

Blood roared in Ishimaru's ears. He took a step backwards, even as he reached into his coat to retrieve his revolver. "What—what do you want?"

Mondo didn't reply immediately. Instead he glanced over his shoulder once more, eying the street below. He held up a hand, forming it into the shape of a gun. He aimed his imaginary weapon downwards, firing it with a faint "ptchoo."

Ishimaru's grip on his hidden gun tightened.

"You had a perfect view from up here, Hall Monitor." Mondo's voice seemed far away, distracted. "Damn good view."

_Kill him, you're being paid big bucks to kill him, kill him now you idiot!_

But something about Mondo's nonchalant tone had him frozen to the spot. His curiosity was too great to ignore.

"What do you want, Oowada?"

Mondo hopped down from the wall, crossing over to Ishimaru in a few swift strides. The bounty hunter stumbled backwards, starting to pull the revolver out fully, but Mondo had grabbed him by the scruff of the neck and pulled him close.

"We need to talk, Hall Monitor."

"About what?"

"About why—" Mondo yanked him closer, eyes boring down on Ishimaru, "—I'm not dead yet."

Ishimaru was more prone to mental freezes than he would ever like to admit. And at that moment, with Mondo glaring daggers at him and his words ringing through his ears, his mind promptly forgot how to function (not the best trait for any bounty hunter).

"I…I…I…I…"

His stammering continued on for a minute, ending only when Mondo released him. The bigger man stepped back towards the edge of the wall, scowling down at the street. "What? Were you too busy jerking off up here to shoot?"

That snapped Ishimaru out of his stupor. He snapped to attention with his own glower. "I'd never!"

"Yeah, I figured as much." Mondo chuckled, a low, throaty chuckle that wasn't very amused at all. "So, after all these years….the one guy who had a clear shot at me didn't take it. And it wasn't through any fuckin' effort of mine. Too much of a pussy?" He threw the comment over his shoulder towards Ishimaru, who bristled but did not reply. Mondo snorted and turned back to his impromptu companion once more. "I've got questions for you, Hall Monitor. And you better answer."

His hidden gun felt heavy and hot against his chest. Ishimaru considered drawing it, firing, but he couldn't entertain the notion for long, because Mondo had withdrawn his own gun and tossed it to the ground. It landed with a clatter some feet away. "Not interested in killing you, Hall Monitor. Too much effort away." He flashed another macabre grin, waiting for Ishimaru to respond.

Slowly the bounty hunter withdrew his own gun. He set it on the rooftop, much more carefully than Mondo had his, and kicked it away. It went spinning off to join the gangster's.

He breathed out before glancing back towards Mondo. "What do you want, Oowada?"

"I already told you, numb-nuts, I've got questions for you."

They began to circle each other in a predatory fashion. Despite the temporary truce, both tensed in fight-or-flight instinct as they carefully moved around the rooftop, eyes fixed on each other. Mondo spoke first:

"Right about now I should be locked in some godforsaken freezer waitin' to be picked apart by a coroner. Instead, I'm here. Question is: why?"

"Do you have a death wish?"

"This ain't twenty questions. Answer me."

"I'll answer yours if you answer mine. It's only fair."

Ishimaru noted the temporary flicker of emotion across Mondo's face. Here was a man who had expected to die, and yet had not, and now was expected to reveal some enormous truth he had hoped to die with him. Ishimaru, sensing his momentary advantage, risked a step closer to Mondo.

The gangster glowered. "For weeks now I've been hearing rumors. Tellin' me some fucker has it out for me, tellin' me I gotta watch my back because there might be a bullet in it if I don't. I've survived before…what, you didn't think you had the honor of being the first to take a shot at the legendary Mondo Oowada, did you?" He smirked as surprise flicked over Ishimaru's features. "No. But those other attempts…those, I survived because I was stronger than they were. But you? You got the jump on me. I didn't see you comin', 'til the last second, and then…" he trailed off, his smirk sliding away. "Nothin'. I didn't survive because I was better than you. I survived because you didn't have the balls to shoot. That's no way to be a man—surviving off of other people's pity."

He spat the last word out as though it were something disgusting. Ishimaru felt bile rise in his throat. "I don't pity you, and I certainly didn't yesterday night. You're a criminal, and you deserve to die—GARGH!"

Mondo had struck out, unexpectedly, and punched Ishimaru in the jaw. The smaller, skinnier man went flying backwards, howling as fiery pain exploding across his jaw. The coppery taste of blood was in his mouth.

Through the ringing in his head he heard Mondo roaring at him and he reflexively jumped out of the way, snapping his leg up and into Mondo's stomach as the bigger man's momentum carried him forward.

Mondo crumpled, swearing, and Ishimaru's boot smashed into his temple. He collapsed on his side, grunting as Ishimaru straddled him. "You," Ishimaru spat, "cheated."

"You should've seen that comin'." Mondo's teeth were stained red as he leered up at Ishimaru. He grimaced as Ishimaru's hands locked around his throat, squeezing slightly.

"You want to know why you're still alive?" Ishimaru snarled. "Because you were doing the public a favor."

And just like that the hands came off of Mondo's throat. Ishimaru's weight came off of his chest.

Ishimaru stood, dusted himself off, and gave his swelling jaw a good rub before continuing for the suddenly speechless Mondo: "You could have let those ruffians drive off drunk. You could have let them kill other people through their recklessness! But you didn't. You did a favor to the public. So I did a favor by letting you live."

The words coming out of his mouth were cold, logical, and followed a simple train of thought: Mondo had done a good deed, and a good deed had been done unto him.

To tell Mondo the truth of the matter—to tell him that seeing a criminal perform such a selfless act had rendered him immobile and conflicted—would have been too much.

Ishimaru turned his back on Mondo, striding over to retrieve his gun, and for that reason it took him a bit longer to hear the soft laughter behind him.

Mondo had crawled up to rest on his elbows and knees. Blood trickled down from his mouth, splattering the ground as he laughed. He wrenched himself up onto his knees, grinning at Ishimaru. "Still just a fuckin' glorified hall monitor. You thought I was doing that for the good of the public? I don't give two shits about the public, man."

And there it was again—that hot, wrenching confusion and muted horror that overwhelmed Ishimaru. His gun was idle in his hands.

Mondo used his overlarge sleeve to wipe some of the blood from his chin. He looked Ishimaru up and down, as if he didn't know what to do with him—despite the fact that he was the one kneeling on the ground and Ishimaru was the one with the gun.

"You're an odd one, Kiyotaka. That much I remember from high school. So, you gonna kill me now or what?"

His name. Mondo remembered his name?!

Ishimaru swallowed hard. "I—"

"BOSS!"

The iron door behind Ishimaru banged open. He had just enough time to pivot on his heel, to start to raise his gun in defense, before a very small, very angry bug bit him in the head.

**…**

The crack of gunfire in the distance sent Kazuichi Souda to his feet. His hair—an ugly, garish pink—swung around him in a curtain as his head darted from side-to-side, looking for the source. "D-did you hear that?"

"Yes. Calm down, will you?" Gundam Tanaka leaned back against the metal stairwell he was sitting on, picking absentmindedly at a cuticle.

Souda bit at his well-worn and stubby fingernails. "What if it's…_her_?" He glanced around again, as if expecting someone to burst from the shadows of the alleyway they had parked themselves in.

"Then she is a complete fool for showing up here when Oowada is nearby," Tanaka snorted. "Oowada is fully capable of destroying her. And if he fails…I will take his place!" He began to flex and un-flex a bandage-covered hand, flashing Souda a sadistic grin.

"Quit the act, man, everybody knows you can't do black magic." Souda shook his head in a resigned sort of way. He began to pace back and forth in front of his motorcycle. "Think the Boss is okay?"

"He can handle himself."

"Yeah, but if he gets himself killed doin' something stupid…" Souda's voice trailed off.

Mondo Oowada was currently the only person in the world who could keep himself and Tanaka safe. And if Oowada was suddenly and violently indisposed…he and Tanaka were done for.

Tanaka grunted and hoisted himself up off of the stairwell, tugging at his scarf. "I'll be right back."

"Wha—where are you going?!"

"To answer nature's call, of course!" Tanaka rolled his eyes as the skittish Souda jumped forward. "Unless you wish to accompany me and be in awe of my manhood…"

Souda shuddered. "Don't call it that! Gross, man. _Gross_." He turned away, pretending he didn't hear Tanaka's soft laughter as the animal breeder-slash-mage-slash-gangster rounded the corner. He took to biting his fingernails again, occasionally twitching at some noise in the dark alley.

It hadn't been a gunshot, Souda attempted to assure himself, it had been a car backfiring. Or some kids setting off bottle rockets. Maybe something big had just fallen over. Not a gunshot. There was no danger here.

All of his nails had been worn to fine nubs by the time he realized Tanaka had been gone for far too long.

He'd probably gotten distracted by some stray cat, Souda reasoned, or maybe a pigeon with a broken wing. Tanaka was always wandering off after animals like that.

Still…

Still, there was silence around Souda, the heavy, oppressive silence that predators used to their advantage. The hair on his neck and arms stood at full attention and his breathing hitched. "TANAKA!"

He started forward, shoving his hands into his pockets. "TANAKA, YOU BASTARD, THIS ISN'T FUNNY! WHERE'RE YOU!? Look, I'm sorry I said that you can't do black magic! You totally can, man, honest! You're the best wizard ever! T-Tanaka?—TANAKA!"

Tanaka lay sprawled among trash, blood oozing from his forehead. And over him stood a figure hidden in the shadows, a female figure whose wicked grin shone in the darkness. Around her prowled masked people who focused their gaze on Souda as he took a step backwards, instinct taking over even though he knew he had nowhere to run.

"I—I—"

"Good evening, Kazuichi. Haven't you missed us?"

**…**

He was quite convinced he was dead.

So when he finally wrenched open his eyes and the full profile of Makoto Naegi stared down at him, the first sensation that overwhelmed him was crushing despair.

"Oh, Naegi. You're dead too?"

That earned a laugh from the apparition, who shook his head. "Not quite. Welcome back to the land of the living."

Ishimaru stared at Naegi, and then at the glaringly white ceiling past Naegi. "I'm in the hospital."

Naegi's mouth twitched upwards. "Very good."

"Why am I in the hospital?"

"Someone dumped you by the front entrance. You were unconscious and bleeding pretty badly. The good news is, you're gonna live and you've got quite the scar to show off."

Following the movement of Naegi's eyes, Ishimaru reached up and fingered the stitches running along the side of his head. He'd only been grazed by a bullet, then. Not dead.

A breath of relief escaped him before he looked back to the similarly-relieved Naegi. "What are you doing here?"

"I'm first in your emergency contacts."

"I didn't put you in my emergency contacts!"

"No. Kirigiri did."

Ishimaru snorted and muttered under his breath about Kirigiri respecting the public's right to privacy. Secretly he was glad for the company.

Naegi tilted his head to the side. "D'you wanna tell me what happen?"

"No."

Naegi nodded (Ishimaru had always liked that quality about Naegi—he knew when to leave things alone) before snapping his fingers. "Oh, this note was with you. For your eyes only." He withdrew it from his pocket and handed it off to Ishimaru.

There was an unspoken acknowledgment that Naegi had already read the note, but Ishimaru was willing to let things slide for his only friend. At least, just once.

He flipped the note open, scanning the words with a furrowed brow and gritted teeth:

_You made a man's promise, Hall Monitor._

_Catch me if you can._

_p.s.: You got blood on my coat and you owe me for dry-cleaning._

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What do you mean Gundam shouldn't be in a gang what do you mean I was just sneaking in my favorite boyo from SDR2 ahah what no that's crazy.

Thanks for reading!


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